When he invited me back to his apartment, I felt torn.His promises of expensive shoes and trips to the Caribbean weren’t all that enticing, but I still wanted to fact-check his wealth. Hank led me on a tour of his apartment, which was every bit as luxurious as I’d expected, with floor-to-ceiling views of Manhattan and expensive art on the walls.Another had a fetish for submissives and wanted to pay me ,500 a month to help him realize his fantasies.An attractive couple wrote me seeking a regular “third.” By the time Darrell, a divorced man in his late 40s worth between million and 0 million, contacted me, I was relieved to hear from a potentially worthy candidate.The rest of Hank’s profile, which told me that he was middle-aged, played sports, and worked in finance, was of less interest.We set up a date and specified what we’d be wearing so that we could recognize each other—a navy-blue baby-doll dress and black tights for me, a striped button-down and a maroon cashmere vest for him.If I had a hefty allowance from a generous benefactor, though, I figured that I could take the leap comfortably. To overcome my reservations about walking the line between dating and prostitution, I told myself that any such concerns were the result of societal conditioning.
My companion, a wealthy finance type, was telling me all about himself and posing questions that suggested he was interested in me.
I was frustrated with my job, which offered little upward mobility, and was thinking about quitting it to pursue my goal of becoming a full-time freelance writer.
Holding me back were my lack of savings and my fear of sacrificing a regular paycheck. So what if I had to tap into my inner geisha to secure a patron?
The first thing I noticed when I met Darrell for cocktails at the So Ho Grand Hotel was that his appearance did not match what his profile had advertised.
He’d said he had brown hair, but he was almost completely bald; his body type was more teapot than “athletic”; and he was several inches shorter than he had claimed.